#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/22/2212260.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2212260
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo,  Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
2,6,8-Trimethyl-3,5-bis(methylsulfanyl)benzo[1,2-b:5,4-b']difuran
_journal_coeditor_code           IS2144
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o662
_journal_page_last               o663
_journal_paper_doi               10.1107/S1600536807000785
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H16 O2 S2'
_chemical_formula_moiety         'C15 H16 O2 S2'
_chemical_formula_sum            'C15 H16 O2 S2'
_chemical_formula_weight         292.40
_chemical_name_systematic
;
2,6,8-Trimethyl-3,5-bis(methylsulfanyl)benzo[1,2-b:5,4-b']difuran
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.479(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.895(3)
_cell_length_b                   13.008(5)
_cell_length_c                   14.498(6)
_cell_measurement_reflns_used    5039
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.70
_cell_volume                     1441.6(10)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8031
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.54
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.367
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0664P)²+1.1009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1349
_reflns_number_gt                2702
_reflns_number_total             3097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2144.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -p_2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2212260
_cod_database_fobs_code          2212260
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.16417(8) 0.13072(5) 0.01430(4) 0.03434(18) Uani d . 1
S S2 0.19226(7) 0.64068(4) 0.04782(4) 0.03309(18) Uani d . 1
O O2 0.67414(19) 0.55739(11) 0.17686(10) 0.0264(3) Uani d . 1
O O1 0.64796(19) 0.18436(11) 0.16212(10) 0.0270(3) Uani d . 1
C C1 0.3653(3) 0.17953(16) 0.07964(13) 0.0266(4) Uani d . 1
C C2 0.4143(3) 0.28718(15) 0.09559(13) 0.0230(4) Uani d . 1
C C3 0.3269(3) 0.38103(15) 0.07452(13) 0.0249(4) Uani d . 1
H H3 0.2094 0.3845 0.0423 0.030 Uiso calc R 1
C C4 0.4261(3) 0.46921(15) 0.10468(13) 0.0234(4) Uani d . 1
C C5 0.3902(3) 0.57913(16) 0.09933(13) 0.0255(4) Uani d . 1
C C6 0.5414(3) 0.62742(15) 0.14272(14) 0.0262(4) Uani d . 1
C C7 0.6027(3) 0.46116(15) 0.15430(13) 0.0234(4) Uani d . 1
C C8 0.6950(3) 0.37021(15) 0.18017(14) 0.0251(4) Uani d . 1
C C9 0.5907(3) 0.28482(16) 0.14686(13) 0.0238(4) Uani d . 1
C C10 0.5073(3) 0.12257(15) 0.12071(14) 0.0271(4) Uani d . 1
C C11 0.5902(3) 0.73707(17) 0.15837(15) 0.0316(5) Uani d . 1
H H11A 0.6805 0.7532 0.1270 0.038 Uiso calc R 1
H H11B 0.6321 0.7499 0.2254 0.038 Uiso calc R 1
H H11C 0.4896 0.7793 0.1329 0.038 Uiso calc R 1
C C12 0.8811(3) 0.36481(17) 0.23901(18) 0.0364(5) Uani d . 1
H H12A 0.9588 0.3625 0.1976 0.055 Uiso calc R 1
H H12B 0.8965 0.3041 0.2778 0.055 Uiso calc R 1
H H12C 0.9066 0.4244 0.2791 0.055 Uiso calc R 1
C C13 0.5402(3) 0.01050(17) 0.13009(16) 0.0342(5) Uani d . 1
H H13A 0.5757 -0.0076 0.1963 0.041 Uiso calc R 1
H H13B 0.6311 -0.0076 0.0998 0.041 Uiso calc R 1
H H13C 0.4351 -0.0260 0.1002 0.041 Uiso calc R 1
C C14 0.0312(3) 0.1401(2) 0.09831(19) 0.0424(6) Uani d . 1
H H14A -0.0842 0.1150 0.0695 0.064 Uiso calc R 1
H H14B 0.0245 0.2107 0.1166 0.064 Uiso calc R 1
H H14C 0.0825 0.0997 0.1537 0.064 Uiso calc R 1
C C15 0.0642(3) 0.6019(2) 0.12901(16) 0.0371(5) Uani d . 1
H H15A -0.0509 0.6310 0.1088 0.056 Uiso calc R 1
H H15B 0.1196 0.6259 0.1920 0.056 Uiso calc R 1
H H15C 0.0559 0.5283 0.1295 0.056 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C14 102.27(11) n
C5 S2 C15 100.38(11) n
C7 O2 C6 106.54(16) n
C9 O1 C10 106.58(16) n
C10 C1 C2 107.42(18) ?
C10 C1 S1 125.39(17) ?
C2 C1 S1 127.11(16) ?
C3 C2 C9 120.28(18) ?
C3 C2 C1 135.09(19) ?
C9 C2 C1 104.58(17) ?
C4 C3 C2 116.20(18) ?
C4 C3 H3 121.9 ?
C2 C3 H3 121.9 ?
C3 C4 C7 120.44(18) ?
C3 C4 C5 134.74(19) ?
C7 C4 C5 104.81(17) ?
C6 C5 C4 107.06(18) ?
C6 C5 S2 125.09(17) ?
C4 C5 S2 127.85(16) ?
C5 C6 O2 111.16(18) ?
C5 C6 C11 133.0(2) ?
O2 C6 C11 115.79(19) ?
O2 C7 C8 123.56(18) ?
O2 C7 C4 110.42(17) ?
C8 C7 C4 126.00(18) ?
C7 C8 C9 111.10(18) ?
C7 C8 C12 124.32(18) ?
C9 C8 C12 124.55(18) ?
O1 C9 C8 123.80(18) ?
O1 C9 C2 110.27(17) ?
C8 C9 C2 125.92(19) ?
C1 C10 O1 111.14(18) ?
C1 C10 C13 133.4(2) ?
O1 C10 C13 115.43(19) ?
C6 C11 H11A 109.5 ?
C6 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C6 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C8 C12 H12A 109.5 ?
C8 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C8 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C10 C13 H13A 109.5 ?
C10 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C10 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
S1 C14 H14A 109.5 ?
S1 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
S1 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
S2 C15 H15A 109.5 ?
S2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
S2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.752(2) n
S1 C14 1.800(3) n
S2 C5 1.749(2) n
S2 C15 1.804(2) n
O2 C7 1.378(2) n
O2 C6 1.383(3) n
O1 C9 1.382(2) n
O1 C10 1.381(3) n
C1 C10 1.351(3) ?
C1 C2 1.456(3) ?
C2 C3 1.398(3) ?
C2 C9 1.405(3) ?
C3 C4 1.396(3) ?
C3 H3 0.9300 ?
C4 C7 1.404(3) ?
C4 C5 1.456(3) ?
C5 C6 1.356(3) ?
C6 C11 1.480(3) ?
C7 C8 1.391(3) ?
C8 C9 1.395(3) ?
C8 C12 1.505(3) ?
C10 C13 1.481(3) ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C11 H11B Cg1 2_655 0.96 2.75 3.480(3) 133
C13 H13A Cg3 2_645 0.96 2.82 3.586(3) 138
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C14 S1 C1 C10 102.73(19)
C14 S1 C1 C2 -80.81(19)
C10 C1 C2 C3 -177.3(2)
S1 C1 C2 C3 5.8(3)
C10 C1 C2 C9 0.4(2)
S1 C1 C2 C9 -176.55(14)
C9 C2 C3 C4 1.8(3)
C1 C2 C3 C4 179.2(2)
C2 C3 C4 C7 -0.8(3)
C2 C3 C4 C5 -179.22(19)
C3 C4 C5 C6 179.5(2)
C7 C4 C5 C6 0.9(2)
C3 C4 C5 S2 -0.4(3)
C7 C4 C5 S2 -178.94(14)
C15 S2 C5 C6 -111.48(19)
C15 S2 C5 C4 68.37(19)
C4 C5 C6 O2 -0.4(2)
S2 C5 C6 O2 179.48(13)
C4 C5 C6 C11 178.4(2)
S2 C5 C6 C11 -1.7(3)
C7 O2 C6 C5 -0.3(2)
C7 O2 C6 C11 -179.32(16)
C6 O2 C7 C8 -177.59(18)
C6 O2 C7 C4 0.9(2)
C3 C4 C7 O2 -179.98(16)
C5 C4 C7 O2 -1.2(2)
C3 C4 C7 C8 -1.5(3)
C5 C4 C7 C8 177.34(18)
O2 C7 C8 C9 -179.25(16)
C4 C7 C8 C9 2.4(3)
O2 C7 C8 C12 2.5(3)
C4 C7 C8 C12 -175.8(2)
C10 O1 C9 C8 178.53(18)
C10 O1 C9 C2 -0.2(2)
C7 C8 C9 O1 -179.89(16)
C12 C8 C9 O1 -1.7(3)
C7 C8 C9 C2 -1.3(3)
C12 C8 C9 C2 176.9(2)
C3 C2 C9 O1 177.98(16)
C1 C2 C9 O1 -0.1(2)
C3 C2 C9 C8 -0.7(3)
C1 C2 C9 C8 -178.84(18)
C2 C1 C10 O1 -0.6(2)
S1 C1 C10 O1 176.45(13)
C2 C1 C10 C13 179.1(2)
S1 C1 C10 C13 -3.9(3)
C9 O1 C10 C1 0.5(2)
C9 O1 C10 C13 -179.22(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125396
